US5516460A - Detergent compositions comprising aldobionamides - Google Patents

Detergent compositions comprising aldobionamides Download PDF

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US5516460A
US5516460A US08/518,902 US51890295A US5516460A US 5516460 A US5516460 A US 5516460A US 51890295 A US51890295 A US 51890295A US 5516460 A US5516460 A US 5516460A
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nonionic
aldobionamide
hydrogen
aldobionamides
surfactant
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Van Au
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Lever Brothers Co
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Lever Brothers Co
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/86—Mixtures of anionic, cationic, and non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the present invention relates to detergent compositions comprising aldobionamides as nonionic surfactant.
  • Aldobionamides and compositions containing aldobionamides are known in the art, for example, from applicants' copending application, U.S. Ser. No. 07/981,737 now U.S. Pat. No. 5,389,279.
  • U.S. Pat. No. 5,389,279 to Au et al. describes binary active detergent active compositions in which nonionic aldobionamides are used in combination with anionic surfactants (e.g., linear alkybenzene sulfonates or LAS) instead of combinations of LAS and the high alkoxylated nonionic surfactants (e.g., Neodol 25-7, a nonionic surfactant from Shell having a C 12 -C 15 alkyl group and alkoxylated with average seven alkylene oxide groups). That is, U.S. Pat. No. 5,389,279 compares LAS/Aldobionamide surfactant system relative to LAS/high EO nonionic systems.
  • anionic surfactants e.g., linear alkybenzene sulfonates or LAS
  • high alkoxylated nonionic surfactants e.g., Neodol 25-7, a nonionic surfactant from Shell having
  • the aldobionamides could be used as replacements for low alkoxylated nonionic surfactants (i.e., having average degree of alkoxylation from 1 to 5) in surfactant systems comprising such low EO nonionics; and, in fact, their successful use as replacement for high alkoxylated nonionic surfactants teaches away from the use as low alkoxylated nonionic replacer.
  • aldobionamides are used in a tertiary surfactant system as a replacement for low alkoxylated nonionic surfactants, they function in a far superior manner to the low alkoxylated nonionics normally used (i.e., those nonionic surfactants having an average degree of alkoxylation of from about 1 to 5). That is, there is a synergy between a system comprising (1) anionic plus (2) a mixture of (a) high EO nonionic and (b) lactobionamide while there is no such detergent synergy for a system comprising anionic and a mixture of (a) high EO nonionic and (b) low EO nonionic.
  • lactobionamides can be used to replace "low" alkoxylated nonionics in tertiary systems additionally comprising (1) an anionic surfactant and (2) a high alkoxylated nonionic surfactant (i.e., having average degrees of alkoxylation of 6 and up) to provide a detergency synergy not observed when known low alkoxylated nonionic surfactants were used in the same system.
  • anionic/high EO/lactobionamide systems provide synergy not seen in anionic/high EO/low EO systems.
  • FIG. 1 shows detergency results for various chain length lactobionamides when anionic LAS (linear alkyl aryl sulfonate, e.g., linear alkylbenzene sulfonate) is combined with a mixture of the various chain lengths lactobionamides (LBA) and Neodol 25-7 (Neodol) at ratio of LBA to Neodol of 25:75. Comparative with 25% C 12 EO 3 is also shown. A can be seen, when different chain length LBA is used, there is always detergent synergy. When 25% C 12 EO 3 is used to replace 25% LBA, there is little or no synergy.
  • anionic LAS linear alkyl aryl sulfonate, e.g., linear alkylbenzene sulfonate
  • Neodol 25-7 Neodol
  • FIG. 2 is same as FIG. 1, but ratio of LBA to Neodol is 50:50. Again, when C 12 EO 3 , is used in place of LBA, there is little or no synergy.
  • FIG. 3 is same as FIG. 1, but ratio of LBA to Neodol is 75:25. The same lack of synergy is observed using C 12 EO 3 .
  • FIG. 4 is same as FIG. 1, but using maltobionamide (MBA) wherein ratio of MBA to Neodol is 25:75.
  • MBA maltobionamide
  • synergy is not absent, it is still much greater for mixture when maltobionamide is used with Neodol rather than C 12 EO 3 .
  • FIG. 5 is same as FIG. 4, but ratio of MBA to Neodol is 50:50.
  • FIG. 6 is same as FIG. 4, but ratio of MBA to Neodol is 75:25.
  • FIG. 7 is a more directed comparative intended to show that LAS/aldonamide/high EO yields synergies not seen with LAS/aldonamide/Low EO.
  • aldonamide is with high EO nonionic, there is a synergy (see FIG. 3), but when aldonamide is with low EO nonionic (FIG. 7), there is no synergy whatsoever.
  • the present invention relates to detergent compositions comprising at least the following three required components: (1) an anionic surfactant; (2) a nonionic surfactant having an average degree of alkoxylation of 6 and higher, preferably 6 to 10; and (3) an aldobionamide as described in greater detail herein.
  • the amount of aldobionamide used should be equal to or lower than the amount of high alkoxylated nonionic, i.e., preferably from 50% by wt. aldobionamide: 50% by wt. other nonionic to 1% aldobionamide: 99% other nonionic. This is not, however, a requirement of the invention and the invention will work even if the amount of aldobionamide exceeds the amount of other nonionic.
  • Suitable anionic surfactants are usually water-soluble alkali metal salts of organic sulphates and sulphonates having alkyl radicals containing from about 8 to about 22 carbon atoms, the term alkyl being used to include the alkyl portion of higher acyl radicals.
  • suitable synthetic anionic detergent compounds are sodium and potassium alkyl sulphates, especially those obtained by sulphating higher (C 8 -C 18 ) alcohols produced, for example, from tallow or a coconut oil, sodium and potassium alkyl (C 9 -C 20 ) benzene sulphonates, particularly sodium linear secondary alkyl (C 10 -C 15 ) benzene sulphonates; sodium alkyl glycerol ether sulphates, especially those ethers of the higher alcohols derived from tallow or coconut oil and synthetic alcohols derived from petroleum; sodium coconut oil fatty monoglyceride sulphates and sulphonates; sodium and potassium salts of sulfuric acid esters of higher (C 8 -C 18 ) fatty alcohol-alkylene oxide, particularly ethylene oxide, reaction products: the reaction products of fatty acids such as coconut fatty acids esterified with isethionic acid and neutralized with sodium hydroxide; sodium and potassium salts of fatty acid amides of
  • anionic surfactants are described in "Surface Active Agents and Detergents" (Vol. I & II) by Schwartz, Ferry and Bergh, hereby incorporated by reference into the subject application. Any suitable anionic may be used and the examples are not intended to be limiting in any way.
  • the anionic surfactant will comprise 5% to 95% by wt. of the tertiary surfactant system, preferably 25% to 80% by wt.
  • Suitable nonionic surfactants include, ion particular, the reaction products of compounds having a hydrophobic group and a reactive hydrogen atom, for example aliphatic alcohols, acids, amides or alkyl phenols with alkylene oxides, especially ethylene oxide, either alone or with propylene oxide.
  • Specific nonionic detergent compounds are alkyl (C 6 -C 18 ) primary or secondary linear or branched alcohols with ethylene oxide, and products made by condensation of ethylene oxide with the reaction products of propylene oxide and ethylenediamine.
  • the average degree of alkoxylation with the alkylene oxide should be 6 to 10.
  • the degree of alkoxylation is of course the number of alkylene oxide groups on the molecule.
  • the nonionic surfactant will comprise 5% to 95% by wt. of the tertiary active system, preferably 20% to 75% by wt.
  • the nonionic surfactant should comprise 50% or less of the total of nonionic and lactobionamide used together. This is not a requirement, however, and the compositions may still comprise aldobionamide and nonionic wherein there is more nonionic relative to aldobionamides.
  • the final component of the tertiary surfactant system is the aldobionamide. This is itself a nonionic although different than the nonionic described above.
  • Aldobionamides are defined as the amide of an aldobionic acid (or aldobionolactone) and an aldobionic acid is a sugar substance (e.g., any cyclic sugar comprising at least two saccharide units) wherein the aldehyde group (generally found at the C 1 position of the sugar) has been replaced by a carboxylic acid, which upon drying cyclizes do an aldonolactone.
  • an aldobionic acid is a sugar substance (e.g., any cyclic sugar comprising at least two saccharide units) wherein the aldehyde group (generally found at the C 1 position of the sugar) has been replaced by a carboxylic acid, which upon drying cyclizes do an aldonolactone.
  • An aldobionamide may be based on compounds comprising two saccharide units (e.g., lactobionamides or maltobionamides from the aldobionamide bonds), or they may be based on compounds comprising more than two saccharide units, as long as the terminal sugar in the polysaccharide has an aldehyde group.
  • an aldobionamide must have at least two saccharide units and cannot be linear.
  • Disaccharide compounds such as lactobionamides or maltobionamides are preferred compounds.
  • Other examples of aldobionamides (disaccharides) which may be used include cellobionamides, melibionamides and gentiobionamides.
  • aldobionamide which may be used for purposes of the invention is the disaccharide lactobionamide set forth below: ##STR1## wherein R 1 and R 2 are the same or different and are selected from the group consisting of hydrogen; an aliphatic hydrocarbon radical (e.g., alkyl groups and alkene groups which groups may contain heteroatoms such as N, O or S or alkoxylated alkyl chains such as ethoxylated or propoxylated alkyl groups), preferably an alkyl group having 8 to 24, preferably 10 to 18 carbons; an aromatic radical (including substituted or unsubstituted aryl groups and arenes); a cycloaliphatic radical; an amino acid ester, ether amines and mixtures thereof, except that R 1 and R 2 cannot be hydrogen at the same time.
  • R 1 and R 2 are the same or different and are selected from the group consisting of hydrogen; an aliphatic hydrocarbon radical (e.g., alkyl groups and alkene groups which groups may contain
  • Suitable aliphatic hydrocarbon radicals include saturated and unsaturated radicals including but not limited to methyl, ethyl, amyl, hexyl, heptyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, allyl, undecenyl, olelyl, linoleyl, linolenyl, propenyl, and heptenyl.
  • Aromatic radicals are exemplified, for example, by benzyl.
  • Suitable mixed aliphatic aromatic radicals are exemplified by benzyl, phenyl ethyl, and vinyl benzyl.
  • Cycloaliphatic radicals are exemplified by cyclopentyl and cyclohexyl.
  • aldobionamides used in the composition of the invention have surprisingly been found to be useful as a replacement for alkoxylated nonionic surfactants having low average degree of alkoxylation (i.e., 1-5); and have further been found to provide detergent synergy when used in the tertiary active systems of the invention relative to the use of the same systems where low alkoxylated nonionic surfactants are used instead of aldobionamides.
  • a lactobionamide of the invention was made as follows:
  • aldobionamides of the invention e.g., lactobionamides
  • anionic and the other nonionic i.e., high alkoxylated nonionic
  • the performance of the aldobionamide was evaluated as a mixed system (ratio of LBA to Neodol was 25% to 75%; 50% to 50% or 75% to 25% and percentages of LAS:Nonionic combined was also 25% to 75%; 50% to 50% and 75% to 25%) at about 0.22 g/L total surfactant.
  • a non-phosphate, zeolite built burkite (sodium carbonate) base powder comprising about 0.45 g/L of commercially available zeolite powder (Zeolite 4A) and 0.30 g/L sodium carbonate was dosed over the side at about 1.0 g/L.
  • the ratio of total surfactant to zeolite base powder was about 22%.
  • the system was kept at 37° C., pH 10, 120 ppm hardness (added as 2:1 ratio of Ca:Mg) for 15 minutes.
  • Detergency improvement was measured as a change in reflectance ( ⁇ R) of the stained cloth before and after washing with the detergent prototype as measured in a standard reflectometer. In general, larger reflectance values suggest better detergency and oily soil removal.
  • linear alkylbenzene sulphonate (LAS) (anionic) was mixed with 1 to 100% by wt. of a mixture of lactobionamide (LBA) and Neodol 25-7 (a nonionic having average degree of ethoxylation of 7 and C 12 -C 15 average claim length) such that ratio of LAS to Neodol was 25% to 75%.
  • LBA lactobionamide
  • Neodol 25-7 a nonionic having average degree of ethoxylation of 7 and C 12 -C 15 average claim length
  • Example 2 is similar to Example 1, but wherein ratio of aldobionamide to high alkoxylated nonionic is 50:50. There the superiority of aldobionamides over low alkoxylated nonionic (when used to replace) is shown in every case. This is seen from FIG. 2.
  • Example 3 is like Example 1 and 2 except ratio of aldobionamide to high alkoxylated nonionic is 75:25. This is seen in FIG. 3. As in FIG. 2, the superiority of aldobionamide as a replacement for a low alkoxylated nonionic is seen in every case.
  • Example 4 is like Example 1 except it teaches a ratio of maltobionamide rather than lactobionamide to high alkoxylated nonionic of 25:75. The superiority of aldobionamides over low alkoxylated nonionic is shown in every case.
  • Example 5 is like Example 4 except the ratio of maltobionamide to high alkoxylated nonionic is 50:50.
  • Example 6 is like Example 4 except the ratio of maltobionamide to high alkoxylated nonionic is 75:25.
  • Example 7 shows that when aldobionamide is used to replace the high EO nonionic surfactant to form an anionic/aldobionamide/Low EO nonionic surfactant system, there is no synergy whatsoever.

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  • Engineering & Computer Science (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
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EP (1) EP0754216B1 (fr)
AU (1) AU2110295A (fr)
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DE (1) DE69503490T2 (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5786468A (en) * 1995-03-24 1998-07-28 Lever Brothers Company, Division Of Conopco, Inc. Anionic glycasuccinamide surfactants and a process for their manufacture

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Publication number Priority date Publication date Assignee Title
AU7738096A (en) * 1995-11-14 1997-06-05 Case Western Reserve University Saccharide surfactants
GB0106466D0 (en) 2001-03-15 2001-05-02 Unilever Plc Fabric softening compositions

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US2752334A (en) * 1952-03-01 1956-06-26 Nat Dairy Res Lab Inc Nu-substituted lactobionamides
US3988433A (en) * 1973-08-10 1976-10-26 The Procter & Gamble Company Oral compositions for preventing or removing stains from teeth
EP0550106A1 (fr) * 1991-12-31 1993-07-07 Unilever N.V. Procédé de production d'aldonamides N-substitués
EP0550281A2 (fr) * 1991-12-31 1993-07-07 Unilever Plc Compositions contenant des tensioactifs glycolipidiques non-ioniques
WO1994003468A1 (fr) * 1992-08-06 1994-02-17 S.A. A.T.T.A. Applications Et Transferts De Technologies Avancees Composes amphiphiles derives d'acides amines ou de peptides, leurs procedes de synthese et leur application comme systemes d'apport de medicament
US5310542A (en) * 1991-12-31 1994-05-10 Lever Brothers Company, Division Of Conopco, Inc. Oral hygiene compositions containing antiplaque agents
WO1994012511A1 (fr) * 1992-11-25 1994-06-09 Unilever Plc Aldonamides et leur utilisation comme tensioactifs
US5336765A (en) * 1991-12-31 1994-08-09 Lever Brothers Company, Division Of Conopco, Inc. Process of preparing N-substituted aldobionamides
US5401839A (en) * 1993-03-23 1995-03-28 Lever Brothers Company, Division Of Conopco, Inc. Process of preparing N-substituted aldonamides having improved color and color stability
US5416075A (en) * 1993-11-30 1995-05-16 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Biospecific emulsions
US5433883A (en) * 1993-11-04 1995-07-18 Lever Brothers Company, Division Of Conopco, Inc. Toilet bar compositions comprising nonionic glycolipid surfactants and polyalkylene glycol structurant

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US3988433A (en) * 1973-08-10 1976-10-26 The Procter & Gamble Company Oral compositions for preventing or removing stains from teeth
US5296588A (en) * 1991-12-31 1994-03-22 Lever Brothers Company, Division Of Conopco, Inc. Process of preparing N-substituted aldonamides
EP0550281A2 (fr) * 1991-12-31 1993-07-07 Unilever Plc Compositions contenant des tensioactifs glycolipidiques non-ioniques
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WO1994012511A1 (fr) * 1992-11-25 1994-06-09 Unilever Plc Aldonamides et leur utilisation comme tensioactifs
US5401839A (en) * 1993-03-23 1995-03-28 Lever Brothers Company, Division Of Conopco, Inc. Process of preparing N-substituted aldonamides having improved color and color stability
US5433883A (en) * 1993-11-04 1995-07-18 Lever Brothers Company, Division Of Conopco, Inc. Toilet bar compositions comprising nonionic glycolipid surfactants and polyalkylene glycol structurant
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5786468A (en) * 1995-03-24 1998-07-28 Lever Brothers Company, Division Of Conopco, Inc. Anionic glycasuccinamide surfactants and a process for their manufacture
US5844103A (en) * 1995-03-24 1998-12-01 Lever Brothers Company, Division Of Conopco, Inc. Anionic glycasuccinamide sufactants and a process for their manufacture

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EP0754216A1 (fr) 1997-01-22
AU2110295A (en) 1995-10-30
EP0754216B1 (fr) 1998-07-15
CA2181702A1 (fr) 1995-10-19
DE69503490T2 (de) 1998-12-10
ES2121412T3 (es) 1998-11-16
DE69503490D1 (de) 1998-08-20

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